1995–2003: Early supporting roles Olyphant's first paid acting job was in a 1995
WB television pilot based on
77 Sunset Strip.
Phyllis Huffman cast him in the role but he did not have an opportunity to meet the show's producer,
Clint Eastwood, who quit days before filming began. Later that year, he made his professional
Off Broadway debut in the
Playwrights Horizons' production of
The Monogamist and received the
Theatre World Award for Outstanding Debut Performance. He starred in the world premiere of
The SantaLand Diaries (1996) at the
Atlantic Theater Company, a one-man play based on
David Sedaris' essay about working as a
Macy's department store Christmas elf.
Ben Brantley of
The New York Times felt the "charming" Olyphant did "a wonderful job" when imitating other characters but had "a harder time finding a convincing style for the running narrative".
Howard Kissel of
The New York Daily News remarked that he delivered "all the drollery with a perfect deadpan and a twinkle" while David Patrick Stearns of
USA Today described him as "an excellent young actor who successfully projects the world-weariness of a young 20-something who slowly evolves into somebody who just might believe in Christmas." Olyphant made his feature film debut in
The First Wives Club (1996) as an eager young director who attempts to cast Elise Elliot (
Goldie Hawn) – who thinks she will be playing the leading lady – in the role of the elderly mother. Airing on the same day of that film's release, he made his television debut in the pilot of the
CBS spy series
Mr. & Mrs. Smith. In 1997, Olyphant made a guest appearance as Officer Brett Farraday in three episodes of the
ABC police drama
High Incident and returned to New York's Playwrights Horizons to play a supporting role in
Plunge. He also had minor roles in the romantic comedy
A Life Less Ordinary and the CBS television film
Ellen Foster. Olyphant's most high-profile role of 1997 was as a film student later revealed as one of the killers in the successful horror film
Scream 2, bringing "a degree of wild-eyed flair to the role," according to
HitFix's Chris Eggertsen. He later described the role as "a gift. I had virtually nothing on my resume at that point. I'm sure some of it was made up." Also that year, he had supporting roles in the HBO war film
When Trumpets Fade and the independent ensemble drama
1999. Two little-seen films were released in 1999: the drama
Advice from a Caterpillar, in which Olyphant played the bisexual love interest of
Cynthia Nixon's character, and the offbeat ensemble comedy
No Vacancy, in which he starred with
Christina Ricci. Olyphant received positive notices for portraying a drug dealer in the cult comedy
Go (1999).
Janet Maslin of
The New York Times noted that the role was "played with offbeat flair" while
Todd McCarthy of
Variety described it as a "deftly etched" performance. He was set to star in the fantasy film
Practical Magic, but he was replaced by
Aidan Quinn. After Olyphant's performance in
Go, the film's producer
Mickey Liddell offered him his choice of parts in his next project
The Broken Hearts Club (2000), a romantic comedy about a group of gay friends living in West Hollywood.
The Village Voices
Dennis Lim commented that his leading performance was better than the film deserved: "Olyphant is charismatic enough for his worst lines not to stick." However,
Mick LaSalle of the
San Francisco Chronicle felt he played the part "like a straight actor gaying it up". Olyphant played a detective in the successful action film
Gone in 60 Seconds (2000) and joked in an interview about the challenges of playing "second fiddle to a car"; his performance reminded
The Washington Posts
Stephen Hunter of a young
Bill Paxton. Olyphant was offered a starring role for a character called
Dominic Toretto in another car film called
Redline – that would later be retitled
The Fast and the Furious. According to Sony producer
Neal H. Moritz, "The studio said, 'If you can get Timothy Olyphant to play that role we will greenlight the movie.'" Olyphant declined the role, which went to
Vin Diesel. The film went on to be a massive success with
nine sequels to date. Olyphant later discussed passing on a lot of roles earlier in his career. In 2011, when asked by
The Hollywood Reporter what was the most absurd project he had ever been pitched, he replied, "I've passed on absurd projects and they have become enormous, enormous hits spawning numerous sequels, and I'm not in them." In 2018, he reflected on passing on the role of Toretto in
The Fast and the Furious, thinking it would be "stupid" and would bomb at the box office. Olyphant also had supporting roles in the musical comedy
Rock Star, and the romantic comedy
Head Over Heels (all 2001). He starred in the short film
Doppelganger (2001) and appeared in an episode of the
Sci-Fi Channel horror series
Night Visions (2002). The independent drama
Coastlines made its debut at the 2002
SXSW Festival, but failed to find a distributor until 2006. Olyphant starred opposite
Josh Brolin as an ex-con who returns to his Florida hometown to collect a $200,000 debt. Kevin Crust of the
Los Angeles Times wrote that he "possesses the kind of thousand-yard stare that suggests something deeper going on," while
Owen Gleiberman of
Entertainment Weekly remarked that "Olyphant, in the sort of role that
Paul Newman used to swagger through, has a star's easy command." However, Todd McCarthy of
Variety felt his performance "sort of floats along". Olyphant's most high-profile role of 2003 was in
A Man Apart, an action film starring Vin Diesel.
Desson Howe of
The Washington Post remarked that Olyphant "gets a kudo or two for [having] the good sense to realize he's playing one of the movie's many one-dimensional characters, so he might as well have insane fun". Similarly, Mick LaSalle of the
San Francisco Chronicle noted that "the most lively character in "A Man Apart" turns out [to be] a middling drug dealer played to the hilt by Timothy Olyphant." He appeared in the
film adaptation of
Stephen King's horror novel
Dreamcatcher as one of four friends attacked by parasitic aliens. The film was poorly reviewed, with David Rooney of
Variety remarking: "Only
Lee and Olyphant come close to hitting the right note of tongue-in-cheek humor that might have made all this palatable. Unfortunately, they're the first to go." Also in 2003, he appeared in the independent ensemble drama
The Safety of Objects. Olyphant received widespread praise for his 2004 performance as a porn film producer in the comedy
The Girl Next Door. He was initially reluctant to audition for the part, feeling it was too similar to some of his previous roles but, "as my manager dutifully reminded me, not many people saw those movies."
A.O. Scott of
The New York Times remarked that the part was played with "a throwaway inventiveness" while
Kenneth Turan of the
Los Angeles Times felt it was played "with wonderful comic zest".
David Edelstein of
Slate enjoyed his "spaced-out volatility. Olyphant's Kelly is a brilliant synthesis of poses."
Joe Leydon of
Variety said he "strikes an impressively deft balance of hearty amiability and understated menace in his scene-stealing turn". In a 2015 interview, Olyphant reflected on the early stages of his film career, and not getting the leading roles that would have possibly led to major fame: "I got great opportunities right off the bat. And at the same time I either passed or failed to get things that would have made things ridiculously quick. I passed on enormous opportunities only to end up playing the supporting role in the next film. And then I'd think to myself, "What the fuck am I doing? Why did I do that?" But sometimes I feel like I got away with some things, because I've been able to work for a long time and I haven't had to deal with any kind of fame issues."
2004–2009: Deadwood and leading film roles Olyphant came to the attention of a wider audience when he was cast as Sheriff
Seth Bullock in HBO's acclaimed western
Deadwood, which aired for three seasons from 2004 to 2006.
Deadwood gave him the opportunity to play a righteous, brooding lawman. The show's creator,
David Milch, said of the casting choice: "Bullock's uprightness is an alternative to going medieval on people. You can see that same fire and that possibility in Tim, even at his most genial ... I'm not sure which poet talked about 'thoughts too deep for words,' but he brings that idea alive ... Tim is a guy that doesn't let himself be known easily." While Bullock was initially introduced as
Deadwoods protagonist,
Emily VanDerWerff of
The A.V. Club noted that the character of
Al Swearengen came to "dominate the show ... This is not to slight Timothy Olyphant. He's a fine actor, and his portrayal of Bullock is frequently very, very good. Bullock is still unquestionably one of the most important characters on the show but the character of a Wild West lawman, no matter how revisionist it was in its portrayal of that lawman as someone who seemed barely in control at all times, just ended up not having as much to do in a blatantly revisionist Western about how chaos gives way to civilization." Matt Feeney of
Slate described Bullock as "laconic, feral, hot-tempered and a little vain", and said the character was "not so much played as embodied by Olyphant".
Alan Sepinwall of HitFix found his performance "fierce and commanding" while Jeremy Egner of
The New York Times said that he showed "a capacity for explosive, nuanced performance barely suggested by earlier roles". He has been somewhat critical of his own performance: "Frankly, the show is much better than my performance ...
Ian was like a little kid, playing with the props and playing with the language and he never lost the sense of fun of it all. I wasn't operating at that same level." Also in 2006, he made a guest appearance in an episode of the
NBC comedy
My Name Is Earl. In 2007, Olyphant starred in the romantic comedy
Catch and Release. He knew co-star
Jennifer Garner from their days as struggling actors in New York, and was excited for the opportunity to play a romantic lead. Lael Loewenstein of
Variety felt "Olyphant clearly has a bright future" while
Desson Thomson of
The Washington Post described him as "the strongest performer here" but that he was "entirely misplaced, an estimable actor caught in a thankless, frilly role". Scott Tobias of
The A.V. Club remarked: "Olyphant's trademark volatility makes him a livelier romantic lead than the usual stuffed shirt." Similarly,
Stephanie Zacharek of
Salon found him "effective here precisely because he seems a little sharp and dangerous. He's not your typical cuddly romantic lead." Olyphant's first post-
Deadwood roles were the action movies
Live Free or Die Hard and
Hitman (both 2007). (
Coastlines was first screened during the Sundance Film Festival in 2002 while
Catch and Release was filmed in 2005.) He had bought a house in the weeks before
Deadwoods cancellation and he later admitted his job choices during this period were for "purely financial reasons". Both he and
Bruce Willis have said his role was underwritten in the script, and he enjoyed working with Willis to develop the character.
Peter Travers of
Rolling Stone declared him "a master at smiling menace", while Mick LaSalle of
The San Francisco Chronicle found him "perfectly ice cold". However,
Manohla Dargis of
The New York Times remarked: "Mr. Olyphant has many charms, but annihilating menace is not one of them." He next starred in
Hitman, a video game adaptation, as the assassin
Agent 47. He was hired to replace Vin Diesel six weeks before filming began and reluctantly agreed to shave his head. The film was commercially successful, grossing over $100 million, but received negative reviews. Todd McCarthy of
Variety described Olyphant as "an actor capable of portraying subtle ambiguities and thought, which suggests he ought to branch out to play something other than baddies". Nick Schager of
Slant Magazine was disappointed to see the actor "reduced to glowering and posing with pistols" while Manohla Dargis of
The New York Times felt he was "strangely, at times ridiculously, miscast". In 2008, he had a supporting role as a
lieutenant colonel in the
Iraq War drama
Stop-Loss, played a pompous newscaster in the little-seen comedy
Meet Bill, voiced the character Cowboy in the video game
Turok and made a guest appearance on the first season of the ABC sitcom
Samantha Who? with
Christina Applegate. Olyphant had a new outlook when choosing his 2009 projects, influenced by his experience with
Hitman: "It motivated me to take a little more responsibility with what I was doing ... I was very fond of the director and a lot of the people that worked on the film but there was definitely a part of me that was like, "What am I doing here?'" He starred as a morphine addict in the little-seen independent heist comedy
High Life, with
Derek Elley of
Variety praising his "terrific" performance. He had a starring role in the thriller
A Perfect Getaway as a possible serial killer of fellow holidaymakers in Hawaii. Manohla Dargis of
The New York Times enjoyed "the regrettably underemployed" actor's performance,
Ty Burr of
The Boston Globe found him "delightfully confident" while
Lisa Schwarzbaum of
Entertainment Weekly noted he "has a heckuva good time telegraphing macho mania". He was nominated for the
Toronto Film Critics Association Award for Best Supporting Actor. He returned to the stage for one night to appear in
Standing on Ceremony: The Gay Marriage Plays, benefiting the
Human Rights Campaign. Also in 2009, he appeared in 11 episodes of the
FX legal thriller
Damages, as a morally ambiguous love interest for
Rose Byrne's character. Byrne later said he was her favorite
Damages guest star, while FX president
John Landgraf sent him the pilot script for another FX project,
Lawman (later renamed
Justified).
Peter Bradshaw of
The Guardian was impressed by the "saturnine screen presence of Timothy Olyphant – that formidable actor who deserves a lead role to match his potential."
The Hollywood Reporters Michael Rechtshaffen found him "convincing" while
Claudia Puig of
USA Today enjoyed the "smart, stoic and sympathetic" performance. He also appeared in the independent comedy
Elektra Luxx (2010).
2010–2015: Justified and comedic performances Olyphant starred in FX's modern-day western series,
Justified, as Deputy U.S. Marshal
Raylan Givens, who is reassigned to his native Eastern Kentucky following a "Justified," but questionable, quick-draw shooting of a criminal in Miami. There, he encounters many outlaw figures from his childhood, including his father and Boyd Crowder, with whom he dug coal as a teenager. Olyphant was initially drawn to "the ease and the charm and the sort of old-fashionedness" of the character The character of Raylan Givens was created by novelist
Elmore Leonard, appearing in his short story "Fire in the Hole" (2001) and the novels
Pronto (1993) and
Riding the Rap (1995). Leonard was an executive producer of
Justified and befriended Olyphant; his final novel,
Raylan (2012), was inspired by the television show. Raylan Givens has been described by many television critics as the "defining role" of Olyphant's career. Brian Lowry of
Variety said it was "an unabashed star turn": "There are surely worse ways to be pigeonholed than playing tough, laconic lawmen, and Timothy Olyphant is carving himself a formidable niche in those confines ... It's an enormously appealing performance." Tim Goodman of the
San Francisco Chronicle praised "an incredibly riveting performance": "Olyphant's steely gaze, Zen interior and matinee looks called to mind a younger Clint Eastwood." Daniel Fienberg of HitFix described him as "a tremendously compelling actor. It's not that he thrives only on minimalism, but he gets a lot out of a little. His performance is about potential energy, or potential violence. And Olyphant does "intense and coiled" to perfection." Matthew Gilbert of
The Boston Globe said: "It's hard to imagine any other actor in the part, as Olyphant milks Raylan's smooth, laconic cowboy style for as much wry humor as he can. He is riveting without a lot of noise — both his body language and his conversation are pared down, and yet his presence is always resonant." Although Olyphant was nominated for a
Primetime Emmy Award for Outstanding Lead Actor in a Drama Series in 2011, he and the show were often perceived to have been "snubbed" by Emmy voters. Matt Zoller Seitz of
Vulture suggested this was because it was "the kind of performance that almost nobody recognizes as 'acting.' It's an old-fashioned movie hero performance in which much of the emotional action is internal and articulated with great subtlety." Similarly, Robert Bianco of
USA Today commented that his "masterfully complete immersion in the role seems to have masked the talent expended playing it". Olyphant also served as a co-executive producer on
Justified, working with
Graham Yost and the writing team on some of the show's storylines and coming to the set on his days off to work with guest stars. Olyphant made occasional guest appearances on comedy television shows during
Justifieds six-season run. He played a paper salesman in two episodes of the NBC comedy
The Office (2010), after
Mindy Kaling, a writer, producer and actress on the show, pushed for him to make a guest appearance. In 2012, he played a character billed as White Sushi Chef in an episode of the FX sitcom
The League (2012) and voiced a character in an episode of the FX animated series
Archer. In 2013, he appeared as a love interest on the
Fox comedy
The Mindy Project. The guest appearance came about after he told Kaling that he wanted to appear on the show and he later said he would have been happy to play his middle-aged skateboarder character for "years". Olyphant also worked on numerous films in between seasons of
Justified. He voiced the Spirit of the West in the animated film
Rango (2011). The character was a parody of
Clint Eastwood's
Man with No Name and Olyphant was cast after director
Gore Verbinski overheard him speaking on television: "I just sort of doubled back and looked through the door and was like, "That's our guy" ... Timothy has such a great quality to his voice." Olyphant appeared as a mentor to
Alex Pettyfer's character in the science-fiction thriller
I Am Number Four (2011). but Betsy Sharkey of the
Los Angeles Times felt he was "an untapped resource". Also in 2011, he voiced a character called Sergeant First Class "Grinch" in the video game,
Call of Duty: Modern Warfare 3. In 2013, he appeared as
Jeff Garlin's father in the independent comedy ''
Dealin' with Idiots and took part in a one-off LACMA Live Read of the black comedy Raising Arizona'' (1987); he played
Nicolas Cage's character while
Amy Poehler played
Holly Hunter's character. In 2014, Olyphant starred with
Tina Fey in the ensemble comedy-drama
This Is Where I Leave You. Their characters were teenage sweethearts until an accident left him with a mild brain injury. The film received mixed reviews, with David Edelstein of
Vulture commenting: "Over the course of his career, Olyphant has given life to head-slappingly bad material, and he does it again by simply underplaying."
2015–present: Santa Clarita Diet, Deadwood and Justified return Olyphant had a recurring guest role as a fictionalized version of himself in the Fox comedy
The Grinder (2015–2016). His performance received positive critical notices, with
USA Todays Robert Bianco declaring it an "Emmy-deserving performance". The role won him the
Critics' Choice Television Award for Best Guest Performer in a Comedy Series. In early 2016, Olyphant starred in the world premiere of
Kenneth Lonergan's comedy
Hold On to Me Darling at the off-Broadway
Atlantic Theater Company. His character, Strings McCrane, is a self-absorbed country singer and actor who returns home to
Tennessee following his mother's death. Ben Brantley of the
New York Times found him "entertainingly irritating" in a performance that "avoids the obvious route of histrionic posing"; "The startling, bona fide sorrow that Mr. Olyphant brings to [the final scene] truly illuminates everything that has come before." Frank Rizzo of
Variety felt his performance was "a stunner, striking just the right notes of guilelessness, obliviousness and narcissism to make Strings one of the most appealing messes in a long time". David Rooney of
The Hollywood Reporter felt the role "seems tailor-made for his laid-back swagger and sly humor ... Olyphant's natural charm ensures that Strings' unapologetic self-absorption remains more human than monstrous." He also played Henry, ex-husband of Sandy (
Jennifer Aniston), in the universally-panned ensemble
romantic comedy ''
Mother's Day'' (2016); he appeared in
Oliver Stone's
Snowden (2016) as a
CIA agent who befriends
whistleblower Edward Snowden just prior to Snowden's fleeing to Russia, after publicly leaking classified US government information. In February 2017, Olyphant began starring in the
Netflix horror-comedy
Santa Clarita Diet, and also served as an executive producer for the series, which co-starred
Drew Barrymore. Netflix renewed the series for a second season in March 2017 and for a third, ultimately final season in May 2018.
Dark Was the Night, an independent drama in which he starred with
Marisa Tomei, was filmed in 2015 and premiered at the 2018
Galway Film Fleadh. In early 2016, HBO announced that David Milch was developing a two-hour film continuation of
Deadwood. The follow-up to the television series began production in October 2018.
Deadwood: The Movie premiered on HBO on May 31, 2019. In 2017, it was reported that Olyphant would play an
FBI agent in the film
Driven, though he ultimately did not appear in the film. In 2018, Olyphant was cast as a voice actor for the
stop-motion animated film
Missing Link, which was released in April 2019. He was also part of the large ensemble cast for the
Quentin Tarantino semi-historical film
Once Upon a Time in Hollywood, which was released in July 2019. Olyphant portrayed TV western star
James Stacy in the film. In 2020, Olyphant joined the
Star Wars franchise when he appeared as
Cobb Vanth in the second season of the
Disney+ space Western The Mandalorian. In 2022, he reprised the role in the first season of
The Mandalorian spinoff series
The Book of Boba Fett. Olyphant returned to the role of Raylan Givens in the 2023 miniseries
Justified: City Primeval. On November 28,
Deadline Hollywood revealed Olyphant has been cast as Kirsh in
Noah Hawley’s upcoming
Alien: Earth. ==Personal life==